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Should the Cubs Ink Cole Hamels to a Multi-Year Deal Right Now? Could They If They Tried?

The Cubs hold a $20 million club option for 2019 on 34-year-old lefty Cole Hamels, who was brilliant with the team after a mid-season trade from the Rangers. We have discussed the option decision at length recently, including the potential luxury tax cap implications, so I won’t re-tread all of the same ground here.

Instead, I want to talk about the possibility that the Cubs lock Hamels down to a multi-year deal before that option decision is due (five days after the World Series ends, so anywhere from the very end of October to November 5).

At a very surface level, a two-year deal worth, say, $24 million sounds like a win-win, right? Cubs get Hamels for two years at a much lower AAV than the option price ($12 million versus $20 million*), and Hamels gets $4 million more in security than he’d be getting if the Cubs just picked up the option. Done deal. Do it.

… except this completely ignores the reality of free agency, which looms for Hamels if he doesn’t re-sign with the Cubs. At age 34, Hamels is set to be a free agent for the first time in his career. He may very well have loved his brief time with the Cubs, but it’s hard to imagine that he loved it enough to want to push out free agency by two more years for just a little bit of extra security.

Isn’t Hamels going to at least want to look around? I’ve gotta think yes, unless the Cubs really step up with a significant multi-year offer. And they may very well want to do so – keeping Hamels around for depth (and upside, given how he looked this year!), and what could prove to be a low AAV on the right deal, could be incredible valuable right now in this competitive window. I very, very much hope the Cubs figure out how to keep Hamels.

But the mechanics of coming up with the right deal in the next three weeks will be very tricky. Let’s imagine that the Cubs have decided they will not be picking up the $20 million option for 2019. That means Hamels would be starting out free agency with a $6 million payment (from the Rangers), buying out that option. If he forgoes that buyout by signing a deal with the Cubs before free agency, that means – if he were simply doing a rational, financial calculation – he’d have to get $6 million more from the Cubs on his deal that he projects himself to get in free agency.

To be sure, Hamels had a very down 2017 season (4.20 ERA, 4.62 FIP, 17.1% K rate, 8.6% BB rate) and a very down first half of 2018 (4.72 ERA, 5.20 FIP, 22.7% K rate, 8.4% BB rate) with the Rangers. He was invigorated with the Cubs, saw his velocity pop and his results improve dramatically (2.36 ERA, 3.42 FIP, 23.4% K rate, 8.1% BB rate), but will that be enough for a pitcher of his age to get a three or four-year deal in free agency worth $15+ million per year? I’m not so sure, even in a free agent class that isn’t loaded with starting pitching options.

Dream scenario? Hamels loved his time with the Cubs and is willing to sign something like a three-year, $30 to 36 million deal. The AAV is relatively low for a starting pitcher, and Hamels locks in an extra $10 to $16 million of security (to the extent that matters to him, given his already substantial career earnings). Much higher than that, and the Cubs may just have to let things play out in free agency, especially given a glut of starting pitchers as it is (Kyle Hendricks, Jon Lester, Jose Quintana, Yu Darvish, Mike Montgomery, Tyler Chatwood, Drew Smyly).

Of course, with a $6 million buyout coming to him if he doesn’t re-sign with the Cubs, sure seems like Hamels could do better than three years and $24 to $30 million in free agency, right? Or, at least, that might be his range and he’d get to at least talk to lots of teams and choose his location. You couldn’t blame him for wanting to see.

(Photo by Mitchell Leff/Getty Images)

The more I’ve thought about this Hamels situation, the more I’ve felt like this is what’s going to happen: these negotiations will occur, but not produce a long-term deal before the option decision is due five days after the World Series ends. The Cubs will decline the option at that time, Hamels will receive his buyout from the Rangers, and he will enter into free agency unfettered for the first time in his career. The Cubs will say – and mean! – that they would love to have him back, and they will stay in touch. But Hamels, as one of the better starting pitchers in the free agent class, will have the opportunity to talk to many teams about where he could play next. If there isn’t a significant suitor early in the process, and if the Cubs maneuver the early part of their offseason the way they want, then perhaps they hang out at the periphery on Hamels (like they did, for one example in a similar situation, with Dexter Fowler a few years ago). If there isn’t a better fit or better deal out there, then maybe the sides sign a multi-year deal later in the offseason.

That is all speculation, informed by my read of the situation. It remains possible that the Cubs simply will pick up the option on Hamels for 2019, and leave it there. It’s probably slightly more than he’d get on a one-year deal in free agency, but he could very well get a multi-year deal worth much more than that. The Cubs may decide a slight overpay for one year is worth it to keep Hamels in-house.

*(As we’ve noted before, all discussions about the price of the option year for 2019 are subject to the caveat that although the Cubs would have to pay out the full $20 million, it may actually only count for $14 million in AAV, since the $6 million buyout was already part of the guaranteed money in his original deal. It’s a little complicated by the mid-season trade and Rangers agreeing to pay that buyout, but increasingly, I’m thinking that Hamels would count only $14 million in AAV for the Cubs next year, which would make the option all the more attractive.)

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